S-(ethylxanthoyl) n, n-diethylamidothiophosphoric chloride



Patented Feb. 9, 1954 I UNITED STATES PATENT OFFICE S (ETHYLXANTHOYL)N,N-DIETHYLAMIDO- THIOPHOSPHORIC CHLORIDE Henry Tolkmith, Midland,Mich., assignor to The Dow Chemical Company, Midland, Mich., acorporation of Delaware No Drawing. Application April 21, 1953, SerialNo. 350,238

2 tion or subtraction of heat it required. Following the reaction, thecrude mixture may be filtered and the filtrate fractionally distilledunder reduced pressure to separate the desired 1? f product. The latteris a water-like liquid boil- C2H5 0 ing at 100 C. at millimeterspressure.

01 02115 In the representative preparation, grams This compound is aviscous oil, somewhat soluble in many organic solvents and substantiallyin soluble in water. It is of value as an interma diate for thepreparation of more complex organic derivatives and as a toxicconstituent of parasiticide compositions,

The new compound may be prepared by react-- ing one molecular proportionof an alkali metal ethylxanthate with one molecular proportion ofdiethylamidophosphoric dichloride of the for- (0.31 mole) of sodiumethylxanthate was added to grams (0.31 mole) of diethylamidophosphoricdichloride dispersed in 150 milliliters of benzene and the resultingmixture heated with stirring for 3 hours at a temperature of 60- C. [itthe end of this period, the reaction product was diluted with an equalvolume of diethyl ether and the resulting mixture filtered. The filtratewas then concentrated by distillation under reduced pressure to atemperature up to 60 C. to obtain as a residue 69 grams of an S- mllla(ethylxanthoyl) N,N diethylamidothiophos- 00H 0 m it phoric chlorideproduct. The latter was an oily H liquid having a density of 1.195 at 18C.

The new S-(ethylxanthoyl) N,N-diethylamidocam 01 thiophosphoric chlorideproduct is effective as a parasiticide and adapted to be employed for inan inert organic solvent such as benzene. In so the control of a widerange of agricultural and practice sodium ethylxanthate is preferablyemhousehold pests such a fli mites, aphids ployed as the alkyli metalxanthate reactant. beetles and cockroaches. For such use, the Incarrying out the reaction of sodium ethylcompound may be dispersed on aninert finely xanthate and diethylamidophosphoric dichloride di id d 11aand employed as a dust. Also, such ar p r d in th v n n th resulting mx- 30 mixtures may be dispersed in water with the ture heated withstirring for a period of time 'at aid f a, dispersing and wetting agentand the a temperature of from 40 to C. Temperaresulting aqueoussuspensions employed as tures substantially in excess of 80 C. for anysprays. In other procedures, the new product ppreciable period of timeshould be avoided as may be employed in oils, as a constituent in oilthedesired product has a tendency to decom at in-water emulsions, or inwater dispersion with D E at u p ature. Upo pletion of or without theaddition of emulsifying, wetting the reaction, the reaction mixture maybe filtered or dispersing agents. Suitable concentrations of and thefiltrate concentrated by distillation under the toxicant in dusts are inthe order of from reduced pressure at gradually increasing about 0.1 toin percent by weight of the dust peratures up to a temperature of 89 C.to sept and in liquid suspensions from about 0.1 to 3 arate low boilingconstituents and to obtain as pounds per gallons of the spray mixture. aresidue the desired S-(ethylxanthoyl) N,N- In representative operationsagainst flies and diethylamidothiophosphoric chloride. cockroaches. 100percent kills these pests are Th i hyl mid pho ph dichloride obtainedwith dust compositions containing 4.5 ployed as a starting material inthe above-do =15 percent by weight of the toxic MN-diethylamidoscribedmethod may be prepared by reacting thiophosphoric chloride. phosphorusoxychloride (P0013) with diethyl- This is a continuation in part ofmycopendamine. Satisfactory yields are obtained when ing applicationSerial No. 203,767, filed Decememploying two molecular proportions ofthe her 30, 1950. amine with each proportion of phosphorus oxyto Iclaim:

chloride. The reaction takes place readily at temperatures of from 0 to40 C. The reaction is somewhat exothermic, the temperature beingcontrolled by regulation of the rate of contacting the reactants as wellas by the addi- S ethylitanthcyil N,Ndiethylaniidothiophosphcricchloride.

HENRY TOLKMITH.

No references cited.

